(E)-1,2-di(2-p-tolylsulfinylphenyl)ethylene | 1029690-30-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: (E)-1,2-di(2-p-tolylsulfinylphenyl)ethylene
• 英文别名: 1,2-bis[(S)-2'-(p-tolylsulfinyl)phenyl]ethane；1-[(S)-(4-methylphenyl)sulfinyl]-2-[(E)-2-[2-[(S)-(4-methylphenyl)sulfinyl]phenyl]ethenyl]benzene
• CAS: 1029690-30-9
• 化学式: C₂₈H₂₄O₂S₂
• 分子量: 456.629
• InChiKey: DZOJTFZBXHQODV-HALAKRJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  32
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  频哪酮 、 (S)-2-(p-toluenesulfinyl)benzyl iodide 在 sodium hexamethyldisilazane 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.02h， 以26%的产率得到(2S,3S)-2-叔丁基-2-甲基-3-[(S)-2-(对甲苯磺酰基)苯基]环氧乙烷
  参考文献：
  名称：

  Stereoselective Alkylidenation of Ketones with 2-(p-Toluenesulfinyl)benzyl Iodide: Synthesis of Enantiomerically Pure Trisubstituted Epoxides

  摘要：

  de Alkylidenation of arylmethyl, dialkyl, and cyclic ketones with 2-(p-toluenesulfinyl)benzyl iodide in the presence of NaN(SiMe3)(2) takes place with a high or complete control of the facial selectivity at the carbonyl group (up to 98% de) and the carbanion (>98% de), respectively, yielding mixtures of only two optically pure trisubstituted epoxides (E/Z ratio ranges between 2:1 and >50:1). Removal of the P-tolylsulfinyl group with t-BuLi provides the corresponding (E)-3-phenyl-2,2-disubstituted epoxides without affecting their optical purity.

  DOI：

  10.1021/ol8005387

文献信息

• Stereoselective Alkylidenation of Ketones with 2-(<i>p</i>-Toluenesulfinyl)benzyl Iodide: Synthesis of Enantiomerically Pure Trisubstituted Epoxides
  作者：Yolanda Arroyo、Ángela Meana、M. Ascensión Sanz-Tejedor、José Luis García Ruano

  DOI：10.1021/ol8005387

  日期：2008.6.5

  de Alkylidenation of arylmethyl, dialkyl, and cyclic ketones with 2-(p-toluenesulfinyl)benzyl iodide in the presence of NaN(SiMe3)(2) takes place with a high or complete control of the facial selectivity at the carbonyl group (up to 98% de) and the carbanion (>98% de), respectively, yielding mixtures of only two optically pure trisubstituted epoxides (E/Z ratio ranges between 2:1 and >50:1). Removal of the P-tolylsulfinyl group with t-BuLi provides the corresponding (E)-3-phenyl-2,2-disubstituted epoxides without affecting their optical purity.